The Pittsburgh Penguins are in a precarious position following their playoff absence last season. They are evaluating their roster and considering trades to acquire future assets as part of a potential rebuild. Veteran forward Rickard Rakell has attracted interest from several teams, yet his preference is to remain in Pittsburgh. Coming off a career year with 70 points, including 35 goals and 35 assists, trading Rakell could significantly impact the team’s offensive capabilities. Nevertheless, if the Penguins decide to pursue a trade, they aim to find a balance between building for the future and remaining competitive, especially with superstar Sidney Crosby still in the mix.

The Montreal Canadiens are grappling with salary cap challenges as they aim to finalize their roster for the upcoming season. Currently, they face a $5.42 million overage with only restricted free agent Jayden Struble left to sign. The Canadiens are hoping to avoid using Long-Term Injured Reserve (LTIR) for Carey Price, whose contract, owed a $5.5 million bonus soon, could be a target for trade. Teams like the San Jose Sharks and Pittsburgh Penguins may be interested, particularly as they seek to bolster their rosters without exceeding their own cap limits.

The Penguins are also in a precarious situation, looking to shed contracts for younger talent. Rickard Rakell is a player who may be on the move, with potential suitors including the Detroit Red Wings, Los Angeles Kings, and Seattle Kraken. These teams are in need of forwards or defensemen to enhance their lineups. The Penguins face a steep price for Rakell, especially given the dwindling free-agent market, making trades a likely necessity for contentions.

Connor McDavid is in the final year of his contract with the Edmonton Oilers, raising speculation about his future. The Pittsburgh Penguins have been highlighted as a potential destination due to their storied history of star players like Mario Lemieux and Sidney Crosby. Although currently in a rebuilding phase, the Penguins have draft capital and salary cap space to attract top talent. The idea of Crosby and McDavid playing together is enticing for fans, offering a symbolic passing of the torch from one generational talent to another.

General Manager Kyle Dubas emphasizes competitive spirit while Crosby is still active, seeking to build a contender. If the Penguins can show progress in this season, they may well be positioned to make a play for McDavid when he becomes a free agent. Despite the allure of a lucrative contract, the decision will hinge on whether McDavid feels the Penguins can be competitive during his prime.

As the Pittsburgh Penguins face a challenging future after missing the playoffs for three consecutive seasons, speculation about their iconic captain Sidney Crosby's potential departure is intensifying. NHL insider Nick Kypreos hinted that Crosby might be traded after the 2026 Winter Olympics, with the Montreal Canadiens emerging as a possible destination. Kypreos emphasized that Crosby remains too talented to merely guide a struggling franchise, suggesting it would be a disservice to his legacy.

Despite the Penguins' front office indicating they are not considering trades for Crosby or other core veterans, the team’s declining performance and aging roster, highlighted by Evgeni Malkin's impending 39th birthday, raises questions about their future direction. While no concrete trade discussions have been reported, Kypreos hinted that significant changes could be on the horizon, particularly if the Penguins seek to rebuild.

Carter Sanderson, a forward recently selected by the Pittsburgh Penguins in the sixth round of the 2025 NHL Draft, has made history as the first South Dakotan ever to be drafted into the NHL. Sanderson's journey included calls from the Penguins, culminating in the moment he was picked at 169th overall. Despite modest rookie numbers in the USHL, where he scored five goals and assisted on six in 48 games, his coach praised his hockey sense and the impact he made on the ice. Sanderson's upcoming season with the Muskegon Lumberjacks will be crucial as he aims to build on his performance and develop further before joining the University of North Dakota.